Breaking Down Your Business | Small Business | Business Owners | Entrepreneurship | Leadership

What’s In This Episode:

In this continuing series about business decisions, Brad wonders if sometimes he makes his decisions a little too quickly. Jill admits that while she listens to her gut, she also reaches out to members of her team and the Founding Moms Community to get feedback on what she should do. If you've got a community, don't hesitate to ask for their opinions.

Kim O'Hara, an intuitive book coach at A Story Inside, calls in to discuss her dilemma. She coaches clients through an 18-week program to help them find their voice and make their books stronger. She also holds workshops, which people love, but she struggles to get people to enroll. Does she quit doing workshops, even though she loves leading them and she feels called to do it? She wants to double her client load in the coming year, and she's tried everything she can think of to get people to come to the writing workshops - Facebook ads, email campaigns - but it doesn't seem to be working.

Jill suggests that Kim axes the workshops for now; she's obviously more successful in her 18-week program and she should focus on that to get more clients. Brad, however, suggests that she shifts her workshops from in-person to virtual. They then propose that she go on the speaker circuit and get the best of both worlds or film one of her workshops to demonstrate her expertise and get people to see the value.

"Don't make a decision and then starve it for what it needs to be successful." - Brad

Jill and Brad then discuss the top 5 things to do AFTER you make a business decision:

  • Commit to it and communicate it to your team.
  • Make a plan to ensure your decision's success.
  • Monitor progress and use data to see if your decision is going the way you thought it would.
  • Occasionally, revisit your decision if your data is leading you in a different direction.
  • And don't forget to do this...

Want to know what it is? Listen in


  • Kim O'Hara is the founder of A Story Inside. An intuitive book coach, Kim believes that words can change everything.
Direct download: Breaking_Down_Your_Business_EP_247.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

What's the weirdest thing you've ever done to arrive at a business decision? Both Jill and Brad have flipped a coin and consulted a magic eight ball.

"Storytelling is where values are communicated." - Brad

Dr. Laura Mraz, founder of Eyas Landing and Blue Bird Day, calls in to ask how she maintains her company culture while she's growing so rapidly. What started as Eyas Landing, a pediatric services clinic with 4-5 employees has grown into a separate school called Blue Bird Day, and now there are 120 employees between the two. She often hears her employees say, "I wish it was like it was before," and gives examples of how she used to hold weekly staff meetings or have therapists train directly under her. But with the rapid growth, those things just aren't possible anymore.

Brad suggests crafting a purpose statement that very clearly states the values of the company. Furthermore, he suggests that she (along with a core team of people) think of stories that demonstrate those company values that she can share with everyone in the company. Jill adds that it sounds like Laura's employees are looking for connection, and that might mean having smaller groups of employees convene for meetings to get feedback.

"I'm always right." - Jill

Jill and Brad then discuss the top 5 ways to make a business decision:

  • Just try it already. It will help you make an informed decision.
  • Ask everyone you know. Ask everyone you don't know.
  • Put it in a form where you can get more in-depth answers.
  • Personally message people on your social media channels when you're looking for very honest feedback.
  • And this is the thing Jill swears by...

Want to know what it is? Listen in


  • Dr. Laura Mraz is the founder of Eyas Landing, a leading pediatric therapy clinic specializing in Sensory Integration, Early Intervention and relationship-based therapy, and Blue Bird Day,  a preschool and kindergarten designed to foster socialization, sensory regulation and academic learning in children ages 2-9.
Direct download: Breaking_Down_Your_Business_EP_246.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

Have you ever thought about how you make decisions? What is your process for making a business decision? Jill listens to her gut. If you don't have a process, can you improve? Jill throws things at the wall and sees what sticks or doesn't stick, and bases her decision and her feelings on that.

"Hone the gut. Fine tune the feeling." - Jill

Then Jill and Brad hear back from a former guest, Nedra Rezinas, who weighs in on a previous episode. She took maternity leave and relied on her colleagues to cover her clients, and it worked out great for her. A lot of the time, business owners are afraid to take time off because they think something will go wrong; it's very much a control issue. But taking time off helps you be a better business owner. So if you're afraid of taking time off, don't be - it'll work out!

"By reaching out to the experts, they may give me some things to consider that  I haven't thought about." - Brad

Jill and Brad then discuss the top 5 things to do before you make a business decision:

  • Data is your friend. Collect it.
  • Get feedback and opinions. People may see things differently than you do. If your business decision affects other people, if you know how they feel about it, you can use that information to convince them.
  • Where might the decision go wrong? Think about that, and then set up experiments to test it.
  • Reach out to the experts. Has someone done what you're trying to do? What's their advice?
  • And the number one thing Brad does after he's done all those other steps? Jill's amazed.
Direct download: Breaking_Down_Your_Business_EP_245.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

As business owners, there's one overarching thing we have to do: we have to make decisions. Big or small, there is seemingly no end to the things we have to make a call on (that's why Mark Zuckerberg and Steve Jobs famously wore the same thing every day, so they could avoid having to decide what to wear). Sometimes, it's just exhausting.

"One of the rules that I recommend is that no one can work for the family until they've worked for someone else for a few years." - Brad

Former trapeze artist Hannah Sullivan and her wife Jade call into the podcast to discuss one big problem: working with family at their company, Pogo Insurance. Hannah's dad, their boss, is your typical alpha male and constantly wants to be the hero. Some of Hannah's siblings, who also work for the company,  don't do their fair share of work. Overall, the ladies just want to be taken seriously.

Brad says that one solution is to have regular family meetings. Establish ground rules and talk about what's going well (and not so well).  If they can separate out and have Hannah's dad as a mentor or advisor, that might be the best case scenario. If not, the other solution is to work someplace else.

"You can't value other people more than you value your own services." - Jill

Jill and Brad then discuss the top 5 worst business decisions they've made:

  • Signing a contract without reading it.
  • If you're going to put on an event, make sure you promote it.
  • Not charging for speaking or consulting.
  • Scaling the business too quickly.
  • And please, please, please, don't do this...

Want to know what it is? Listen in


  • This episode is sponsored by Warby Parker. Buying glasses can be expensive, annoying, and overwhelming. Warby Parker cuts out the middleman by providing high-quality eyewear at a fraction of the cost - and for every pair you buy, they give away a pair to someone who can't afford them.  How can you try glasses out online? Check out their Home Try-On Program for free and get started to find your perfect pair of glasses.


  • Hannah and Jade Sullivan are the co-founders of Pogo Insurance, an online platform that offers commercial insurance policies for freelancers, consultants and others who are self-employed.
Direct download: Breaking_Down_Your_Business_EP_244.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

If you've made it this far in sticking to your goals, you're on your way to forming a habit! Brad's goal for getting feedback is still going strong; you can help him by filling out this three-question survey.

Are there things that you do every day or every week without fail? For Jill's business, she checks e-mail, social media, and checks up on Founding Mom Exchanges. Brad goes to the gym three times a week (and he tracks it using the Streaks App) and both of them are back on the no-sugar wagon. They made it six months last time; can they go a whole year?

"Sometimes it's easier to create a habit. What's a small thing that you can change that leads you to that goal?" - Brad

Harry Duran, host of Podcast Junkies and creator of FullCast, calls to discuss his problem. He primarily gets business via referrals but wants to know how he can branch out to grow his business. Jill says that it never hurts to ask. If Harry is putting out content via newsletters and social media, he can simply ask people to work with him.

Brad says he can also send out a quarterly advertising email to get the message clearly across. Harry can also reference case studies and show his audience real people who have gotten value from working with him. Additionally, since he's already getting the referrals, ask them for feedback - what made them recommend Harry in the first place?

"Throw an 'ask' into everything you're doing." - Jill

Jill and Brad then discuss the top 5 ways to build a new habit:

  • Make a plan. Consistency is key. Set a time and a trigger to do whatever you're working toward.
  • Prep as much as possible. If you want to go to the gym, pack your bag the night before. Things will just become part of the routine.
  • Download a tracking app like Streaks (mentioned above!) or the Productive App. Or do it the old-fashioned way and write things down.
  • Give yourself a visual cue.
  • And the last thing is that you can always do this...


  • Harry Duran is the host of Podcast Junkies and the creator of FullCast, a full-service, done-for-you podcast production and marketing consultancy. He helps six-figure entrepreneurs amplify their authority and extend their reach through the power of podcasting.
Direct download: Breaking_Down_Your_Business_EP_243.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

Brad's still maintaining momentum on his feedback goal. Please go here and fill out his three-question survey. He'll love you forever.

So you have your goals, but the enthusiasm is waning. How do you get through it? Before he discovered the Streaks App, Brad blocked time on his calendar so that he could work on his goals. He plans around his goal. Jill's all about the accountability buddy (though she's liking the sound of that app, too!).

"I like the idea of check-ins. You can't do it alone." - Jill

Kristy Wallace, CEO of Ellevate Network, calls to ask about what the best practices are for owning your brand. She recognizes that there are similar companies out there - and she thinks that's great. But she worries that if other companies do similarly-named events but they don't have the same quality or structure, that could dilute the power of her brand. She's not coming at it from a malicious standpoint; she's just worked really hard to get Ellevate Network to where it is today.

Jill's take - even though it's not legal advice - is that if Kristy isn't going to take anyone to court, there's no point to trademark or copyright anything. The whole point of trademarking something is that you want to prevent someone else from doing that thing or using that name too. Any lawyer will tell you that, of course, you need to trademark. Bigger companies have trademarks, and filing a trademark may also make you feel important. If she wants to, Jill says that Kristy can put a "TM" mark next to their brand name, meaning that they're filing for a registered trademark.

Brad says that nine times out of ten, a conversation is all that's needed. Something like, "Hey, that looks awfully similar to what I've been doing. I would appreciate it if you called it something different." Additionally, he tells Kristy she can use Copyscape to check for plagiarism.

Overall, Jill says, if you're worried about all of this, you're not focused on building your business. So build your business - no one's going to be able to do it as well as you can.

Jill and Brad then discuss the top 5 ways to maintain your momentum:

  • Find a person in your life that can keep you accountable.
  • Write it down, journal it, or post it to your social networks.
  • Download a tracking app like Streaks (mentioned above!) or the Productive App.
  • When you're working, remove all distractions. Put your tech on Do Not Disturb.
  • And the number one thing? Create this!


  • Kristy Wallace is the CEO of Ellevate Network and is responsible for executing their mission to close the gender achievement gap in business by providing professional women with a global community to lean on and learn from.
Direct download: Breaking_Down_Your_Business_EP_242.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

Are you staying focused on what's important and avoiding the trap of being busy? Brad's trying to stay on top of his goals. In fact, he's serious about getting feedback from others (please go here and answer three questions).

Jill says that busy work allows us to avoid the real things you have to do. You don't realize that you're doing busy work, really, until you step back and take a look at it. Plus, every time you get an email and your endorphins rise, it's telling you, "Oh, I'm being productive."

Brad says that email, especially, is tricky. Some of it is busy work, some of it is actually important, and there's probably a lead or two. Facebook and other social media are just as bad as getting sucked into email. But it's the same thing: you're rarely going to make more money by chatting with people via Messenger.

"There's a lot of busy work that we get ourselves involved in that isn't really making progress on our goals." - Brad

Lloyd Lim calls in and talks about his writing career. He began writing nonfiction books in order to simplify complicated topics for people. Before embarking on writing, he worked for the government, and before that, he worked as a lawyer. But now, he's left the government and is working on rebranding himself. He's worked on a lot of public interest projects, but he's doing a lot of them for free. How does he start moving toward getting paid for the work that he does?

Brad suggests that Lloyd narrows down his expertise into one thing that provides the most value. Jill respectfully disagrees with Brad and says to just start charging. Lloyd explains that he's thought about charging a flat fee for assessment of his clients' problems. But he still needs to identify his target market, what's the problem they have, and what's the solution that he's going to offer.

"I'm a big believer in the accountability buddy." - Jill

Jill and Brad then discuss the top 5 ways to measure progress toward your goals:

  • Break your goal into manageable pieces.
  • Make it a game.
  • Create streaks - how many days in a row have you done your goal? (There's even an app for that.)
  • Form a team and check in with someone else.
  • What's YOUR method of making progress toward your goals? Call us and let us know!


Direct download: Breaking_Down_Your_Business_EP_241.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

Brad and Jill made some goals and now they have to start working on them. It's like a clean slate! A chance to start over! What's Jill going to leave behind for the new year? She's going to try to leave behind massive impatience in her business in 2018. Some of it served her well as an entrepreneur; it even helped her build her businesses. But now, to sustain them, she needs even more patience.

Brad's leaving behind social media (he's trying, anyway). He wants to make it a habit to not look at any social media when he's at home. Jill suggests just removing apps from his phone to make it easier not to check. Good luck, Brad!

"Business is about trust, and if you can't follow through on your commitments, why would I do business at all?" - Brad

Then Brad and Jill have a last-minute guest cancellation, which leads to a discussion about commitments. What is it about commitments that people can't handle? No, it's not the first time that a guest has canceled being on the podcast, but doing so last-minute isn't very considerate. Additionally, doing so means that you miss out on other opportunities (in this case, a chance to promote and get advice!).

So, for 2018... don't be that person. It makes you look bad, professionally.

"Celebrate any progress, even the baby steps, because it's gonna help you move along." - Jill

Jill and Brad then discuss the top 5 ways to make immediate progress on your goals:

  • Skip your emails in the first hour of your workday and do the thing that needs doing the most.
  • Take 5 goals that are important in your business, and write them down so that you see them repeatedly.
  • Move somewhere else; work in a different space. Get that creativity flowing.
  • Celebrate any progress!
  • And the number one way to make immediate progress? Delete this thing!


  • This episode is sponsored by Warby Parker. Buying glasses can be expensive, annoying, and overwhelming. Warby Parker cuts out the middleman by providing high-quality eyewear at a fraction of the cost.  How can you try glasses online? Check out their Home Try-On Program for free and get started to find your perfect pair of glasses.
Direct download: Breaking_Down_Your_Business_EP_240.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

We're welcoming 2018! Brad wants to know if Jill likes goals. She wants to know how Brad defines goals, which he does as "something that you're committing yourself to accomplish in a certain period of time". Jill hates them because she finds specific goals to be too limiting and confining. Weirdly, BRAD AGREES WITH HER. He'd get so wrapped up in his goals, he'd stop noticing that there were other things that needed his attention. But he does think goals are useful, as you utilize different actions when working toward a goal.

"I personally don't think as an entrepreneur, I need goals to drive me." - Jill

Kelley Kitley, author, TEDx presenter and founder of Serendipitous Psychotherapy, calls in for advice on how to take her business to the next level. She wants to get on national radio and TV circuits; she wants more speaking engagements. But she doesn't have the money to hire a PR/marketing person, and wonders if she's being annoying. Jill reminds her that there is no such thing as being annoying in business. It's particularly a stigma with women, but there is absolutely no limit.

Brad wants to know if Kelley would be open to raising her prices; as a therapist, she needs to make more money if she's going to devote some of her time being her own PR person. People often believe that a PR person can do a better job than they would be able to, but if Kelley knows what she wants, and knows where to find them, she doesn't have to spend that expense just yet.

"The thing about pricing is - we charge what we have the confidence to ask for." - Brad

Jill and Brad then discuss the top 5 out-of-the-box goals for the year:

  • Pay attention to how much joy there is in your life. Focus on joy, and see how much you can repeat things that bring you joy day-to-day.
  • Go further with fewer initiatives. You don't need to do ALL the things; just focus on a few things and see if it works.
  • Get sleep. It's so important.
  • Get more feedback, even if you're the boss.
  • And the number one thing? Brad's really doing it this time!

Want to know what it is? Listen in


  • Kelley Kitley is the founder of Serendipitous Psychotherapy, as well as the author of an autobiography, MY self.
Direct download: Breaking_Dwon_Your_Business_EP_239.mp3
Category:Business -- posted at: 3:00am EDT

What’s In This Episode:

Christmas is over, but Jill's not giving up on making eggnog a year-round thing. What are the things they loved most from the holiday? Jill's still basking in the hugs from her daughters (and eggnog), while Brad's happy about the slippers he received.

"If you spend all your time on your personal brand, then the business can never really move away from you." - Brad

Eric Paul Olson, chief marketing officer for Clever Stilettos, an online magazine for women entrepreneurs, calls in to discuss his dilemma. He can't figure out what he wants to devote time to -- his personal brand or the Clever Stilettos brand. He has a team of eight people to help him run Clever Stilettos, but he runs a podcast to go along with the magazine. Furthermore, Eric's also an actor on Chicago Fire and Chicago Med, so Brad and Jill suggest that maybe he should hire someone to help him with Clever Stilettos while he focuses on acting. Jill says that hosting a podcast is great, but he needs to hand it off to the team once he's done lending his time to it. His team can promote on all sides - both the Eric Olson brand AND the Clever Stiletto brand. Brad says that some fans of Eric Olson, the actor, will be interested in the fact that he ALSO has a digital marketing interest. Basically, it comes down to knowing who your audience is and distributing content accordingly.

"I want to pay more attention to my space next year. I used to care less about clutter, but I need more space now." - Jill

Jill and Brad then discuss the top 5 non-money-driven goals for next year:

  • Try to be more present. No technology (phone, laptop - put it away!) - spend some more time with your family instead.
  • Taking more time off.
  • Make your workspace work better for you.
  • SAY NO! Get out of the habit of saying yes to everything.
  • And the number one thing? It's a tough one, but anyone can join in...

Want to know what it is? Listen in


  • Eric Paul Olson is the chief marketing officer of Clever Stilettos, a women's entrepreneurial magazine. He splits his time between podcasting and acting
Direct download: Breaking_Dwon_Your_Business_EP_238.mp3
Category:Business -- posted at: 3:00am EDT